Diastereoselectivity in the reduction of alpha-Oxy- and alpha-amino-substituted acyclic ketones by polymethylhydrosiloxane |
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| Authors: | Nadkarni Durgesh Hallissey James Mojica Carlos |
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| Institution: | Process Development Laboratories, Pfizer Global Manufacturing, Eastern Point Road, Groton, Connecticut 06340, USA. durgesh.nadkarni@pfizer.com |
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| Abstract: | Diastereoselectivity in the reduction of alpha-alkoxy-, alpha-acyloxy-, and alpha-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of alpha-alkoxy, alpha-acyloxy, and alpha-dialkylamino ketones. Reduction of alpha-monoalkylamino ketone proceeded in anti-selective manner with moderate selectivity. The observed selectivity is explained based on Felkin-Anh and Cram-chelate models. |
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